Tebipenem pivoxil

• CAT Number: I002068
• CAS Number: 161715-24-8
• Molecular Formula: C22H31N3O6S2
• Molecular Weight: 497.63
• Purity: ≥95%
• Target: Antibacterial
• Solubility: DMSO 100 mg/mL; Water <1 mg/mL
• Storage: Store at -20°C
• IUPAC Name: 2,2-dimethylpropanoyloxymethyl (4R,5S,6S)-3-[1-(4,5-dihydro-1,3-thiazol-2-yl)azetidin-3-yl]sulfanyl-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate
• InChI: InChI=1S/C22H31N3O6S2/c1-11-15-14(12(2)26)18(27)25(15)16(19(28)30-10-31-20(29)22(3,4)5)17(11)33-13-8-24(9-13)21-23-6-7-32-21/h11-15,26H,6-10H2,1-5H3/t11-,12-,14-,15-/m1/s1
• InChIKey: SNUDIPVBUUXCDG-QHSBEEBCSA-N
• SMILES: O=C1[C@H]([C@H](O)C)[C@]2([H])[C@@H](C)C(SC3CN(C4=NCCS4)C3)=C(C(OCOC(C(C)(C)C)=O)=O)N12

Tebipenem (Cat.No:I002068) is a broad spectrum orally administered antibiotic, from the carbapenem subgroup of beta-lactam antibiotics. It was developed as a replacement drug to combat bacteria that had acquired antibiotic resistance to commonly used antibiotics. Tebipenem is formulated as the ester tebipenem pivoxil due to the better absorption and improved bioavailability of this form. It has performed well in clinical trials for ear infection and looks likely to be further developed in future.

Reference

1:Pediatric community-acquired pneumonia treated with a three-day course of tebipenem pivoxil. Sakata H, Kuroki H, Ouchi K, Tajima T, Iwata S; World/’s First Oral Carbapenem Study Group..J Infect Chemother. 2017 May;23(5):307-311. doi: 10.1016/j.jiac.2017.01.009. Epub 2017 Feb 27. PMID: 28238680
2:[Evaluation of safety and efficacy of tebipenem pivoxil granules for pediatric in pneumonia, otitis media and sinusitis]. Kataoka H, Kasahara H, Sasagawa Y, Matsumoto M, Shimada S.Jpn J Antibiot. 2016 Feb;69(1):53-76. Japanese. PMID: 27290830
3:Antibacterial Properties of Tebipenem Pivoxil Tablet, a New Oral Carbapenem Preparation against a Variety of Pathogenic Bacteria in Vitro and in Vivo. Yao Q, Wang J, Cui T, Yang Z, Su M, Zhao P, Yan H, Zhan Y, Yang H.Molecules. 2016 Jan 6;21(1):62. doi: 10.3390/molecules21010062. PMID: 26751436 Free Article
4:The chromatographic approach to kinetic studies of tebipenem pivoxil. Cielecka-Piontek J, Zalewski P, Paczkowska M.J Chromatogr Sci. 2015 Feb;53(2):325-30. doi: 10.1093/chromsci/bmu063. Epub 2014 Jun 30. PMID: 24981980
5:Good transfer of tebipenem into middle ear effusion conduces to the favorable clinical outcomes of tebipenem pivoxil in pediatric patients with acute otitis media. Sugita R.J Infect Chemother. 2013 Jun;19(3):465-71. doi: 10.1007/s10156-012-0513-5. Epub 2013 Feb 8. PMID: 23393013
6:[Clinical efficacy of tebipenem pivoxil treatment in children with pneumonia, who had no relief despite having administered oral beta-lactam antibiotics]. Sakata H.Jpn J Antibiot. 2011 Jun;64(3):171-7. Japanese. PMID: 21861308
7:Intestinal absorption mechanism of tebipenem pivoxil, a novel oral carbapenem: involvement of human OATP family in apical membrane transport. Kato K, Shirasaka Y, Kuraoka E, Kikuchi A, Iguchi M, Suzuki H, Shibasaki S, Kurosawa T, Tamai I.Mol Pharm. 2010 Oct 4;7(5):1747-56. doi: 10.1021/mp100130b. Epub 2010 Sep 3. PMID: 20735088
8:Investigation of pneumonia-causing pathogenic organisms in children and the usefulness of tebipenem pivoxil for their treatment. Kuroki H, Tateno N, Ikeda H, Saito N.J Infect Chemother. 2010 Aug;16(4):280-7. doi: 10.1007/s10156-010-0053-9. Epub 2010 Mar 31. PMID: 20352278
9:[Convulsive liability of an oral carbapenem antibiotic, tebipenem pivoxil]. Yagi Y, Nawa T, Kurata Y, Shibasaki S, Suzuki H, Kurosawa T.Jpn J Antibiot. 2009 Jun;62(3):241-52. Japanese. PMID: 19882983
10:[Pharmacokinetics of tebipenem pivoxil, a novel oral carbapenem antibiotic, in experimental animals]. Kijima K, Morita J, Suzuki K, Aoki M, Kato K, Hayashi H, Shibasaki S, Kurosawa T.Jpn J Antibiot. 2009 Jun;62(3):214-40. Japanese. PMID: 19882982